Director of Product Pricing & Monetization

About the role

HighLevel is hiring a Director of Product Pricing & Monetization to lead our company-wide approach to pricing, packaging, monetization, and customer research.

This person will help HighLevel answer four critical questions:

• Who are our most important customer segments, and what outcomes are they trying to achieve?

• Which products, capabilities, and services do those customers value most?

• How should we package and price our offerings to align customer value with sustainable company growth?

• How do we create a continuous customer-learning system that improves product, go-to-market, and strategic decisions?

You will sit at the intersection of Product, Finance, Data, Growth, Sales, Customer Success, Marketing, and Operations. You will combine customer research, behavioral data, market intelligence, financial analysis, and experimentation to shape HighLevel’s commercial strategy.

This is not an advisory-only role. You will be expected to develop recommendations, build alignment, support implementation, measure results, and improve decisions based on what we learn.

The role reports to the Chief of Staff and will have significant exposure to HighLevel’s executive leadership team.

What you will own

Pricing and packaging strategy

• Develop a clear, company-wide pricing and packaging strategy across subscription plans, product bundles, add-ons, usage-based capabilities, services, and new product launches.

• Evaluate how HighLevel’s pricing architecture should evolve as the platform expands into new products, customer segments, and monetization models.

• Identify the most appropriate value metrics for different parts of the platform, including where subscription, usage-based, account-based, feature-based, or hybrid pricing models may be appropriate.

• Assess opportunities to improve plan differentiation, feature entitlements, upgrade paths, product bundling, and add-on attachment.

• Build business cases for pricing and packaging changes, including expected impact on acquisition, trial-to-paid conversion, average revenue per customer, expansion, retention, gross margin, and lifetime value.

• Develop principles and guardrails for discounts, promotions, trials, grandfathering, migrations, and price increases.

• Partner with Finance and Data teams to model revenue impact, customer impact, adoption scenarios, and potential risks.

• Create a prioritized monetization roadmap rather than treating pricing as a series of isolated decisions.

Customer research and insights

• Build a continuous customer research program covering prospects, trial users, paying customers, expanded customers, churned customers, agency owners, affiliates, and the businesses operating within agency sub-accounts.

• Establish a clear segmentation framework based on customer needs, behaviors, maturity, business models, use cases, value realization, and willingness to pay.

• Lead qualitative and quantitative research, including customer interviews, surveys, concept testing, win/loss analysis, churn research, behavioral analysis, and willingness-to-pay studies.

• Understand the jobs customers hire HighLevel to perform, the outcomes they value, the alternatives they consider, and the barriers that prevent them from adopting or expanding.

• Create a centralized customer-insights repository so that research is accessible, reusable, and connected to company decisions.

• Develop a regular cadence for sharing insights with Product, Marketing, Sales, Customer Success, and executive leadership.

• Translate research into clear implications for product strategy, roadmap prioritization, positioning, onboarding, customer education, and go-to-market execution.

Experimentation and implementation

• Design pricing, packaging, positioning, and offer experiments with clearly defined hypotheses, target segments, success metrics, and decision criteria.

• Partner with Product, Growth, Engineering, Billing, Legal, Finance, Marketing, Sales, and Customer Success to operationalize approved changes.

• Develop rollout strategies that account for existing customers, new customers, channel partners, affiliates, billing complexity, communications, and customer support.

• Establish guardrails to ensure that monetization initiatives improve business performance without creating unacceptable deterioration in customer trust, conversion, adoption, or retention.

• Build post-launch measurement plans and ensure that each major pricing or packaging decision generates reusable learning.

• Monitor performance across metrics such as trial-to-paid conversion, plan mix, average revenue per customer, add-on attachment, expansion, downgrade rates, churn, net revenue retention, gross margin, and customer lifetime value.

Market and competitive intelligence

• Maintain a structured view of pricing, packaging, positioning, and monetization trends across relevant SaaS, agency technology, CRM, marketing automation, communications, AI, and adjacent software categories.

• Identify changes in customer expectations, competitive offers, business models, and emerging value metrics.

• Distinguish between competitive signals that require action and those that should not influence HighLevel’s strategy.

• Use market intelligence as one input alongside customer value, product strategy, economics, and HighLevel’s long-term differentiation.

Decision-making and organizational leadership

• Establish a cross-functional pricing and monetization operating cadence, including clear decision rights, approval processes, and measurement standards.

• Bring structure to complex decisions where customer needs, product strategy, technical constraints, and financial outcomes may conflict.

• Present recommendations to senior leaders in a clear, commercially grounded, and decision-oriented manner.

• Build alignment across functions while remaining willing to challenge assumptions and surface difficult trade-offs.

• Initially operate as a hands-on leader and, as the function develops, help define and build the right team across pricing, monetization analytics, and customer insights.

• Raise the organization’s overall capability in customer research, pricing strategy, experimentation, and value-based decision-making.

What we are looking for

• 12+ years of experience across SaaS pricing, monetization, product strategy, customer insights, growth strategy, management consulting, corporate strategy, or related roles.

• Significant direct experience leading pricing and packaging decisions for a B2B SaaS, platform, or technology company.

• Demonstrated experience translating customer research and data into changes in product, pricing, packaging, or go-to-market strategy.

• Strong understanding of SaaS business models, including subscription economics, usage-based pricing, expansion revenue, retention, gross margin, and customer lifetime value.

• Experience working with multi-product or multi-tier offerings and navigating the impact of pricing changes on existing and new customers.

• Strong quantitative and financial modeling skills, with the ability to develop scenarios, challenge assumptions, and make recommendations with imperfect information.

• Experience with both qualitative and quantitative research methods, such as customer interviews, segmentation, surveys, willingness-to-pay analysis, concept testing, conjoint analysis, and behavioral data analysis.

• Strong commercial judgment and the ability to balance customer value, growth, simplicity, operational feasibility, and long-term strategy.

• Excellent executive communication skills, including the ability to turn complex analysis into a clear recommendation and decision.

• A highly collaborative working style and a record of influencing Product, Finance, Data, Engineering, Marketing, Sales, and Customer Success leaders.

• Comfort operating in a fast-moving environment where the operating model and analytical foundation may still need to be built.

• A player-coach mentality: equally comfortable defining strategy, conducting customer interviews, reviewing analyses, building a business case, and supporting execution.

Preferred experience

• Experience with product-led growth, free trials, self-serve acquisition, or hybrid product-led and sales-assisted models.

• Experience with agency software, SMB software, CRM, marketing automation, communications, payments, AI products, or vertical SaaS.

• Experience with ecosystems in which the direct customer serves or resells products to another end customer.

• Experience with white-label products, reseller models, marketplaces, channel partners, or multi-sided platforms.

• Experience launching usage-based products or monetizing high-variable-cost capabilities such as communications, payments, infrastructure, or AI.

• Familiarity with SQL, experimentation platforms, business intelligence tools, or product analytics systems.

• Experience building a pricing, customer insights, or monetization function from an early stage.

What success looks like

In the first 90 days

• Develop a clear understanding of HighLevel’s customer segments, current plans, product entitlements, monetization model, customer economics, and decision-making processes.

• Complete an initial assessment of pricing and packaging opportunities, risks, customer pain points, and analytical gaps.

• Establish a customer research agenda across trial users, paying customers, expanded customers, churned customers, agencies, affiliates, and sub-accounts.

• Create an initial pricing and packaging opportunity backlog, distinguishing near-term improvements from longer-term strategic questions.

• Establish a cross-functional pricing and monetization governance process.

Within six months

• Deliver a practical customer segmentation and needs framework that is actively used by Product and go-to-market teams.

• Establish a repeatable customer research and insight-sharing cadence.

• Present a prioritized pricing and packaging roadmap supported by customer evidence, behavioral data, competitive context, and financial modeling.

• Launch or support the launch of the first major pricing, packaging, or monetization initiative.

• Implement reporting that connects pricing decisions to customer and business outcomes.

Within the first year

• Establish a clear and scalable pricing architecture across HighLevel’s core platform, add-ons, and emerging products.

• Build a trusted customer-insights capability that consistently informs product, go-to-market, and strategic decisions.

• Create a repeatable process for researching, testing, launching, and evaluating monetization changes.

• Deliver measurable improvement across one or more key outcomes, such as trial-to-paid conversion, plan mix, average revenue per customer, product attachment, expansion, retention, net revenue retention, or gross margin.

• Build strong organizational confidence that major pricing and product decisions are grounded in customer value, sound economics, and rigorous learning.

Why this role matters

HighLevel’s pricing and packaging decisions influence far more than revenue. They shape which customers we attract, how quickly customers understand the platform, which products they adopt, how agencies build businesses on top of HighLevel, and how effectively we can continue investing in customer value.

This role will help create the customer understanding and commercial discipline required for HighLevel’s next stage of growth.